NO314497B1 - Lipopolyamin i D-, L- eller DL-form, deres fremstilling og anvendelse samtpreparater inneholdende forbindelsene - Google Patents

Lipopolyamin i D-, L- eller DL-form, deres fremstilling og anvendelse samtpreparater inneholdende forbindelsene Download PDF

Info

Publication number: NO314497B1
Authority: NO; Norway
Prior art keywords: compound; group; formula; preparation according; compounds
Prior art date: 1997-05-28

Application number

NO19995808A

Other languages

English (en)

Norwegian (no)

Other versions

NO995808D0 (no

NO995808L (no

Inventor

Gerardo Byk

Catherine Du-Bertret

Daniel Scherman

Original Assignee

Aventis Pharma Sa

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1997-05-28

Filing date

1999-11-26

Publication date

2003-03-31

1999-11-26 Application filed by Aventis Pharma Sa filed Critical Aventis Pharma Sa

1999-11-26 Publication of NO995808D0 publication Critical patent/NO995808D0/no

1999-11-26 Publication of NO995808L publication Critical patent/NO995808L/no

2003-03-31 Publication of NO314497B1 publication Critical patent/NO314497B1/no

Links

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239000000644 isotonic solution Substances 0.000 description 1
150000004715 keto acids Chemical class 0.000 description 1
238000002372 labelling Methods 0.000 description 1
239000000787 lecithin Substances 0.000 description 1
229940067606 lecithin Drugs 0.000 description 1
235000010445 lecithin Nutrition 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
238000003670 luciferase enzyme activity assay Methods 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
210000002751 lymph Anatomy 0.000 description 1
210000004698 lymphocyte Anatomy 0.000 description 1
229910001629 magnesium chloride Inorganic materials 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
210000004379 membrane Anatomy 0.000 description 1
239000012528 membrane Substances 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
244000005700 microbiome Species 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
APBBAQCENVXUHL-UHFFFAOYSA-N n,n-diethylethanamine;2,2,2-trifluoroacetic acid Chemical compound CCN(CC)CC.OC(=O)C(F)(F)F APBBAQCENVXUHL-UHFFFAOYSA-N 0.000 description 1
BLUYEPLOXLPVCJ-INIZCTEOSA-N n-[(1s)-2-[4-(3-aminopropylamino)butylamino]-1-hydroxyethyl]-7-(diaminomethylideneamino)heptanamide Chemical compound NCCCNCCCCNC[C@H](O)NC(=O)CCCCCCNC(N)=N BLUYEPLOXLPVCJ-INIZCTEOSA-N 0.000 description 1
HKUFIYBZNQSHQS-UHFFFAOYSA-N n-octadecyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCNCCCCCCCCCCCCCCCCCC HKUFIYBZNQSHQS-UHFFFAOYSA-N 0.000 description 1
210000005036 nerve Anatomy 0.000 description 1
210000000653 nervous system Anatomy 0.000 description 1
210000004498 neuroglial cell Anatomy 0.000 description 1
210000002569 neuron Anatomy 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
AKRYBBWYDSDZHG-UHFFFAOYSA-N nitrosobis(2-oxopropyl)amine Chemical compound CC(=O)CN(N=O)CC(C)=O AKRYBBWYDSDZHG-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
210000001672 ovary Anatomy 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
210000000496 pancreas Anatomy 0.000 description 1
230000001575 pathological effect Effects 0.000 description 1
229940021222 peritoneal dialysis isotonic solution Drugs 0.000 description 1
150000004986 phenylenediamines Chemical class 0.000 description 1
238000000053 physical method Methods 0.000 description 1
229920001308 poly(aminoacid) Polymers 0.000 description 1
229920000656 polylysine Polymers 0.000 description 1
229910000343 potassium bisulfate Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000004237 preparative chromatography Methods 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
229940107700 pyruvic acid Drugs 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
210000000664 rectum Anatomy 0.000 description 1
238000005932 reductive alkylation reaction Methods 0.000 description 1
PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
108091092562 ribozyme Proteins 0.000 description 1
229920002477 rna polymer Polymers 0.000 description 1
230000009962 secretion pathway Effects 0.000 description 1
238000011894 semi-preparative HPLC Methods 0.000 description 1
210000003491 skin Anatomy 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000010532 solid phase synthesis reaction Methods 0.000 description 1
210000000278 spinal cord Anatomy 0.000 description 1
210000000952 spleen Anatomy 0.000 description 1
239000007921 spray Substances 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
238000003756 stirring Methods 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
UIUJIQZEACWQSV-UHFFFAOYSA-N succinic semialdehyde Chemical compound OC(=O)CCC=O UIUJIQZEACWQSV-UHFFFAOYSA-N 0.000 description 1
HUSAJPUAXWOUQS-UHFFFAOYSA-N tert-butyl N-[2-oxo-16-(tetradecylamino)hexadecyl]carbamate Chemical compound CCCCCCCCCCCCCCNCCCCCCCCCCCCCCC(=O)CNC(=O)OC(C)(C)C HUSAJPUAXWOUQS-UHFFFAOYSA-N 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
210000001550 testis Anatomy 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
210000001541 thymus gland Anatomy 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
238000006257 total synthesis reaction Methods 0.000 description 1
230000002110 toxicologic effect Effects 0.000 description 1
231100000027 toxicology Toxicity 0.000 description 1
230000009261 transgenic effect Effects 0.000 description 1
238000013519 translation Methods 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
230000001228 trophic effect Effects 0.000 description 1
210000004881 tumor cell Anatomy 0.000 description 1
230000001173 tumoral effect Effects 0.000 description 1
238000000825 ultraviolet detection Methods 0.000 description 1
238000011144 upstream manufacturing Methods 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
230000003612 virological effect Effects 0.000 description 1
210000001835 viscera Anatomy 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/127—Synthetic bilayered vehicles, e.g. liposomes or liposomes with cholesterol as the only non-phosphatidyl surfactant
- A61K9/1271—Non-conventional liposomes, e.g. PEGylated liposomes or liposomes coated or grafted with polymers
- A61K9/1272—Non-conventional liposomes, e.g. PEGylated liposomes or liposomes coated or grafted with polymers comprising non-phosphatidyl surfactants as bilayer-forming substances, e.g. cationic lipids or non-phosphatidyl liposomes coated or grafted with polymers
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K48/00—Medicinal preparations containing genetic material which is inserted into cells of the living body to treat genetic diseases; Gene therapy
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/04—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
- C07C279/12—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton being further substituted by nitrogen atoms not being part of nitro or nitroso groups
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N15/00—Mutation or genetic engineering; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification; Use of hosts therefor
- C12N15/09—Recombinant DNA-technology
- C12N15/87—Introduction of foreign genetic material using processes not otherwise provided for, e.g. co-transformation

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
Genetics & Genomics (AREA)
Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Biotechnology (AREA)
Epidemiology (AREA)
Bioinformatics & Cheminformatics (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Zoology (AREA)
Biophysics (AREA)
Wood Science & Technology (AREA)
Biomedical Technology (AREA)
General Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Microbiology (AREA)
Plant Pathology (AREA)
Physics & Mathematics (AREA)
Dispersion Chemistry (AREA)
Biochemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Peptides Or Proteins (AREA)
Medicinal Preparation (AREA)
Micro-Organisms Or Cultivation Processes Thereof (AREA)

NO19995808A 1997-05-28 1999-11-26 Lipopolyamin i D-, L- eller DL-form, deres fremstilling og anvendelse samtpreparater inneholdende forbindelsene NO314497B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR9706549A FR2763943B1 (fr)	1997-05-28	1997-05-28	Composes, leur preparation et leur utilisation pour le transfert d'acides nucleiques dans les cellules
PCT/FR1998/001041 WO1998054130A1 (fr)	1997-05-28	1998-05-25	Composes, leur preparation et leur utilisation pour le transfert d'acides nucleiques dans les cellules

Publications (3)

Publication Number	Publication Date
NO995808D0 NO995808D0 (no)	1999-11-26
NO995808L NO995808L (no)	1999-11-26
NO314497B1 true NO314497B1 (no)	2003-03-31

Family

ID=9507333

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19995808A NO314497B1 (no)	1997-05-28	1999-11-26	Lipopolyamin i D-, L- eller DL-form, deres fremstilling og anvendelse samtpreparater inneholdende forbindelsene

Country Status (17)

Country	Link
US (1)	US6300321B1 (fr)
EP (1)	EP0984925B1 (fr)
JP (1)	JP4467084B2 (fr)
KR (1)	KR20010013029A (fr)
CN (1)	CN1131208C (fr)
AT (1)	ATE284383T1 (fr)
AU (1)	AU738320B2 (fr)
BR (1)	BR9809506A (fr)
CA (1)	CA2290664C (fr)
DE (1)	DE69828045T2 (fr)
FR (1)	FR2763943B1 (fr)
HU (1)	HUP0001937A3 (fr)
IL (1)	IL132951A0 (fr)
NO (1)	NO314497B1 (fr)
PL (1)	PL336983A1 (fr)
WO (1)	WO1998054130A1 (fr)
ZA (1)	ZA984440B (fr)

Families Citing this family (30)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7960540B2 (en)	1999-04-08	2011-06-14	Advanced Cancer Therapeutics, Llc	Antiproliferative activity of G-rich oligonucleotides and method of using same to bind to nucleolin
JP2002541264A (ja)	1999-04-08	2002-12-03	ユーエイビー・リサーチ・ファウンデーション	冨ｇオリゴヌクレオチドの抗増殖活性およびヌクレオリンに結合するためのその使用方法
US8114850B2 (en)	1999-04-08	2012-02-14	Advanced Cancer Therapeutics, Llc	Antiproliferative activity of G-rich oligonucleotides and method of using same to bind to nucleolin
US20020091242A1 (en)	2000-10-11	2002-07-11	Michel Bessodes	Acid-sensitive compounds, their preparation and uses
AU2073002A (en) *	2000-11-29	2002-06-11	Aventis Pharm Prod Inc	Neutral and anionic colloidal particles for gene delivery
US20030134423A1 (en) *	2002-01-04	2003-07-17	Chu Yong Liang	Compounds for delivering substances into cells
WO2003106636A2 (fr) *	2002-06-14	2003-12-24	Mirus Corporation	Nouveaux procedes d'apport de polynucleotides dans des cellules
US7906122B2 (en) *	2003-06-18	2011-03-15	Yissum Research Development Company Of The Hebrew University Of Jersusalem	Sphingoid polyalkylamine conjugates for Hepatitis B virus vaccination
EP1638919B1 (fr) *	2003-06-18	2012-09-26	Biolab Ltd.	Conjugues de polyalkylamines de sphingolipides
GB0413613D0 (en) *	2004-06-17	2004-07-21	Univ London	Small molecule carriers
US7973084B2 (en)	2005-04-28	2011-07-05	Postech Academy-Industrial Foundation	Molecular transporters based on alditol or inositol and processes for the preparation thereof
KR100699279B1 (ko)	2005-04-28	2007-03-23	학교법인 포항공과대학교	당 또는 당 유사체를 골격으로 하는 분자 수송체 및 그의제조방법
WO2007021839A2 (fr) *	2005-08-10	2007-02-22	Johns Hopkins University	Polyamines utiles en tant q'agents therapeutiques antiparasites et anticancereux et en tant qu'inhibiteurs de demethylase specifiques a la lysine
GB0613753D0 (en) *	2006-07-11	2006-08-23	Norwegian Radium Hospital Res	Method
WO2013086354A1 (fr)	2011-12-07	2013-06-13	Alnylam Pharmaceuticals, Inc.	Lipides biodégradables pour l'administration d'agents actifs
HUE060907T2 (hu)	2014-06-25	2023-04-28	Acuitas Therapeutics Inc	Új lipidek és lipid nanorészecske formulációk nukleinsavak bevitelére
PT3313829T (pt)	2015-06-29	2024-07-08	Acuitas Therapeutics Inc	Formulações de lípidos e de nanopartículas lipídicas para a administração de ácidos nucleicos
HRP20230209T1 (hr)	2015-10-28	2023-04-14	Acuitas Therapeutics Inc.	Novi lipidi i lipidne formulacije nanočestica za isporuku nukleinskih kiselina
US12491261B2 (en)	2016-10-26	2025-12-09	Acuitas Therapeutics, Inc.	Lipid nanoparticle formulations
WO2018191657A1 (fr)	2017-04-13	2018-10-18	Acuitas Therapeutics, Inc.	Lipides pour administration d'agents actifs
CN110799492B (zh)	2017-04-28	2023-06-27	爱康泰生治疗公司	用于递送核酸的新型羰基脂质和脂质纳米颗粒制剂
CA3073020A1 (fr)	2017-08-16	2019-02-21	Acuitas Therapeutics, Inc.	Lipides destines a etre utilises dans des formulations nanoparticulaires lipidiques
EP4501322A3 (fr)	2017-08-17	2025-04-16	Acuitas Therapeutics, Inc.	Lipides destinés à être utilisés dans des formulations de nanoparticules lipidiques
WO2019036030A1 (fr)	2017-08-17	2019-02-21	Acuitas Therapeutics, Inc.	Lipides destinés à être utilisés dans des formulations de nanoparticules lipidiques
WO2019036028A1 (fr)	2017-08-17	2019-02-21	Acuitas Therapeutics, Inc.	Lipides destinés à être utilisés dans des formulations nanoparticulaires lipidiques
IL281615B2 (en)	2018-09-21	2026-01-01	Acuitas Therapeutics Inc	Systems and methods for producing lipid nanoparticles and liposomes
CA3116576A1 (fr)	2018-10-18	2020-04-23	Acuitas Therapeutics, Inc.	Lipides pour l'administration de nanoparticules lipidiques d'agents actifs
PT3908568T (pt)	2019-01-11	2024-09-30	Acuitas Therapeutics Inc	Lípidos para a administração de agentes ativos por nanopartículas lipídicas
ES3054438T3 (en)	2020-07-16	2026-02-03	Acuitas Therapeutics Inc	Cationic lipids for use in lipid nanoparticles
CA3242402A1 (fr)	2021-12-16	2023-06-22	Acuitas Therapeutics, Inc.	Lipides destines a etre utilises dans des formulations de nanoparticules lipidiques

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR960705771A (ko) *	1993-11-24	1996-11-08	벤자민 에프 맥그로우	구아니딘의 양쪽친화성 유도체(amphiphilic derivatives of guanidine)
US5777153A (en) *	1994-07-08	1998-07-07	Gilead Sciences, Inc.	Cationic lipids
FR2727679B1 (fr) *	1994-12-05	1997-01-03	Rhone Poulenc Rorer Sa	Nouveaux agents de transfection et leurs applications pharmaceutiques
FR2730637B1 (fr) *	1995-02-17	1997-03-28	Rhone Poulenc Rorer Sa	Composition pharmaceutique contenant des acides nucleiques, et ses utilisations
FR2741066B1 (fr) *	1995-11-14	1997-12-12	Rhone Poulenc Rorer Sa	Nouveaux agents de transfection et leurs applications pharmaceutiques
PT888379E (pt) *	1996-03-01	2001-05-31	Centre Nat Rech Scient	Compostos analogos a familia dos amidinios composicoes farmaceuticas que os contem e suas aplicacoes

1997
- 1997-05-28 FR FR9706549A patent/FR2763943B1/fr not_active Expired - Fee Related
1998
- 1998-05-25 HU HU0001937A patent/HUP0001937A3/hu unknown
- 1998-05-25 BR BR9809506-4A patent/BR9809506A/pt not_active IP Right Cessation
- 1998-05-25 JP JP50031699A patent/JP4467084B2/ja not_active Expired - Lifetime
- 1998-05-25 AT AT98928356T patent/ATE284383T1/de not_active IP Right Cessation
- 1998-05-25 AU AU80221/98A patent/AU738320B2/en not_active Ceased
- 1998-05-25 ZA ZA984440A patent/ZA984440B/xx unknown
- 1998-05-25 WO PCT/FR1998/001041 patent/WO1998054130A1/fr not_active Ceased
- 1998-05-25 CA CA2290664A patent/CA2290664C/fr not_active Expired - Fee Related
- 1998-05-25 KR KR1019997011004A patent/KR20010013029A/ko not_active Ceased
- 1998-05-25 IL IL13295198A patent/IL132951A0/xx unknown
- 1998-05-25 EP EP98928356A patent/EP0984925B1/fr not_active Expired - Lifetime
- 1998-05-25 PL PL98336983A patent/PL336983A1/xx unknown
- 1998-05-25 DE DE69828045T patent/DE69828045T2/de not_active Expired - Lifetime
- 1998-05-25 CN CN98805476A patent/CN1131208C/zh not_active Expired - Fee Related
- 1998-05-25 US US09/424,380 patent/US6300321B1/en not_active Expired - Fee Related
1999
- 1999-11-26 NO NO19995808A patent/NO314497B1/no unknown

Also Published As

Publication number	Publication date
IL132951A0 (en)	2001-03-19
AU8022198A (en)	1998-12-30
ZA984440B (en)	1998-12-10
WO1998054130A1 (fr)	1998-12-03
NO995808D0 (no)	1999-11-26
HUP0001937A2 (hu)	2000-10-28
EP0984925B1 (fr)	2004-12-08
ATE284383T1 (de)	2004-12-15
DE69828045D1 (de)	2005-01-13
DE69828045T2 (de)	2005-12-01
JP2002502388A (ja)	2002-01-22
HUP0001937A3 (en)	2003-10-28
CA2290664C (fr)	2010-04-13
FR2763943B1 (fr)	1999-07-09
CA2290664A1 (fr)	1998-12-03
EP0984925A1 (fr)	2000-03-15
CN1257480A (zh)	2000-06-21
US6300321B1 (en)	2001-10-09
PL336983A1 (en)	2000-07-31
AU738320B2 (en)	2001-09-13
NO995808L (no)	1999-11-26
FR2763943A1 (fr)	1998-12-04
JP4467084B2 (ja)	2010-05-26
BR9809506A (pt)	2000-06-20
KR20010013029A (ko)	2001-02-26
CN1131208C (zh)	2003-12-17

Publication	Publication Date	Title
NO314497B1 (no)	2003-03-31	Lipopolyamin i D-, L- eller DL-form, deres fremstilling og anvendelse samtpreparater inneholdende forbindelsene
JP4999784B2 (ja)	2012-08-15	トランスフェクション剤としてのリポポリアミン及びその医薬的使用
EP0968227B1 (fr)	2003-05-28	Lipides cationiques dimeres sur une base de cystine
AU707947B2 (en)	1999-07-22	Novel amide-based cationic lipids
US6638529B2 (en)	2003-10-28	Amide-based cationic lipids
WO1997003939A9 (fr)	1997-05-22	Nouveaux lipides cationiques a base d'amides
AU8813198A (en)	1999-02-16	Cationic polymers, complexes associating said cationic polymers with therapeutically active substances comprising at least a negative charge, in particular nucleic acids, and their use in gene therapy
AU759301B2 (en)	2003-04-10	New agents for transferring nucleic acids, compositions containing them and their uses
MXPA99010489A (en)	2000-05-01	Compounds, preparation and use for transferring nucleic acids into cells
CZ418599A3 (cs)	2000-02-16	Sloučeniny, způsob jejich přípravy a jejich použití pro přenos nukleových kyselin do buněk
MXPA00008970A (en)	2001-09-07	Novel nucleic acid transfer agents, compositions containing same and uses
CZ20003592A3 (cs)	2001-01-17	Nové sloučeniny vhodné jako činidla pro přenos nukleové kyseliny do buňky, způsob jejich přípravy a farmaceutické přípravky obsahující tyto sloučeniny
MXPA99010765A (en)	2000-09-04	Novel class of nucleic acid cationic transfecting agents